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Grafting of 2-hydroxy-4(2,3-epoxypropoxy)-benzophenone and epoxidized soybean oil to wood: Reaction conditions and effects on the color stability of Scots pine
SP Technical Research Institute of Sweden.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-3201-5138
SP Technical Research Institute of Sweden.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
2012 (English)In: Polymer degradation and stability, ISSN 0141-3910, E-ISSN 1873-2321, Vol. 97, no 9, 1779-1786 p.Article in journal (Refereed) Published
Abstract [en]

This study investigates the photostabilizing effect of the reactive UV-absorber 2-hydroxy-4(2,3-epoxypropoxy)-benzophenone (HEPBP) when used as a primer for wood. The present work further includes a study on the effect of HEPBP used in combination with an epoxy functionalized vegetable oil as a primer system. The study is based on reactions performed on pine veneers using 3-pentanone as a solvent and 4-(dimethylamino)pyridine (DMAP) as a catalyst, varying the reaction time and temperature. Results from FTIR and SEC measurements indicate that a desired reaction between HEPBP and wood does occur and that there are synergetic effects when HEPBP and oil are combined. Color measurements also indicate that the use of HEPBP and epoxidized soybean oil as pretreatment for wood results in a lower color change after 400 h of artificial weathering. We conclude that using HEPBP in combination with epoxy functionalized soybean oil does improve photostability of wood exposed to artificial weathering.

Place, publisher, year, edition, pages
2012. Vol. 97, no 9, 1779-1786 p.
Keyword [en]
UV-protection, 2-Hydroxy-4(2, 3-epoxypropoxy)-benzophenone (HEPBP), Wood, Epoxy functionalized soybean oil, Grafting
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-92248DOI: 10.1016/j.polymdegradstab.2012.06.006ISI: 000308051500027Scopus ID: 2-s2.0-84864606912OAI: oai:DiVA.org:kth-92248DiVA: diva2:513009
Note

QC 20121009. Updated from submitted to published.

Available from: 2012-03-30 Created: 2012-03-30 Last updated: 2017-12-07Bibliographically approved
In thesis
1. Enhancing UV-protection of clear coated wood by utilizing reactive UV-absorber and epoxyfunctionalized soybean oil
Open this publication in new window or tab >>Enhancing UV-protection of clear coated wood by utilizing reactive UV-absorber and epoxyfunctionalized soybean oil
2012 (English)Licentiate thesis, comprehensive summary (Other academic)
Abstract [en]

This work presents the development of a new pretreatment for clear coated wood, that aims to increase the photoprotection of exterior wood products, and at the same time make the system more environmentally friendly. The pretreatment comprises the reactive UV absorber 2-hydroxy-4(2,3-epoxy­propoxy)-benzophenone (HEPBP), which has a primary epoxy group that can be covalently attached to the hydroxyl groups of the wood substrate. This reactant is accompanied by renewable epoxy functionalized soybean oil (ESBO), which contains a secondary epoxy group that also has the ability to react with the substrate and that promotes the compatibility between the two reactants. The ESBO further seems to have the advantage of increasing the flexibility of the pretreated veneers as well as decreasing the amount of water in the cell wall of the wood. The study was performed in two parts where the first part focused solely on the development and performance of the pretreatment, whereas the second part used the knowledge gained from part one to evaluate the pretreatment in combination with an acrylic clear coating. Grafting reactions were performed on thin wood veneers heated in solvent. In the first part the reaction parameters, temperature and reaction time, were varied to study their effects on the final properties of the pretreatments. The veneers where then analyzed using FTIR to determine if grafting was achieved. Results show that grafting was successful for reactions performed at temperatures above 90 °C. For part two, grafting was successful for both the boil- and dip process, indicating that a considerably shorter reaction time can be used. Samples from both part one and two where then exposed to accelerated ageing and the color change was measured to estimate the UV-resistance. The first part showed improved UV-resistance for some of the pretreatments, whereas the second part was more difficult to evaluate due to the top coat, but a slight improvement can be seen for samples using the pretreatment. A positive result for part two is also that the pretreatment do not appear to affect the adhesion between the substrate and the top coat. It is hence concluded that the proposed pretreatment is a possible way of increasing the photostability of exterior wood.

Abstract [sv]

Detta arbete beskriver utvecklandet av en ny förbehandling för klarlackat trä som syftar till att öka UV-beständigheten av träprodukter för utomhusbruk. Arbetet syftar även till att utveckla systemet till att bli miljövänligare än nuvarande liknande produkter på marknaden. Förbehandlingen utnyttjar primära epoxidgrupper hos den reaktiva UV-absorbenten 2-hydroxy-4(2,3-epoxy­propoxy)-bensofenon (HEPBP) för att skapa kovalenta bindningar till hydroxylgrupper hos träet. Den andra komponenten i systemet är förnyelsebar epoxiderad sojaolja (ESBO) innehållande sekundära epoxidgrupper som även dessa kan binda kovalent till träytan, samt gynna kompatibiliteten mellan de två reaktanterna. Oljan verkar dessutom öka flexibiliteten av förbehandlingen, samtidigt som den minskar mängden vatten som tränger in i cellväggen. Studien utfördes i två delar där den första delen fokuserade enbart på att utveckla förbehandlingen, medan den andra delen utnyttjade information från den första delen för att utvärdera funktionen av förbehandlingen i kombination med en akrylatbaserad klarlack. Ympningsreaktionerna utfördes på tunna träfaner i uppvärmd lösning. I första delen studerades hur temperatur- och reaktionstidsförändringar påverkar den slutgiltiga prestationen av förbehandlingen, och FTIR användes då för att verifiera ympningen. Resultaten visar att ympningen var lyckad för reaktioner utförda vid reaktionstemperaturer över 90 °C. För del två ansågs ympningen lyckad för både dopp- och kokreaktionen, vilket tyder på att betydligt kortare reaktionstider skulle kunna användas. Prover från både del ett och två utsattes sedan för accelererad åldring där färgförändringen av proverna mättes för att uppskatta UV-resistensen av behandlingarna. Första delen visade på ökad UV-beständighet för vissa av behandlingarna. Del två var dock svårare att utvärdera till följd av klarlacken, men en liten förbättring kan noteras för prover som är förbehandlade. En positiv notering från del två är även att adhesionen mellan klarlacken och träytan inte verkar ha påverkats av förbehandlingen. Med detta som grund dras slutsatsen att den föreslagna förbehandlingen kan förbättra UV-resistensen av klarlackat trä för utomhusbruk.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2012. 47 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2012:17
Keyword
UV-protaction, wood, clear coating, UV absorber, epoxy functionalized soybean oil, grafting
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-92220 (URN)978-91-7501-292-6 (ISBN)
Presentation
2012-04-27, E3, Osquars backe 14, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
Formas, 2008-1447
Note
QC 20120330Available from: 2012-03-30 Created: 2012-03-29 Last updated: 2012-03-30Bibliographically approved
2. Enhancing UV protection of clear coated exterior wood by reactive UV absorber and epoxy functional vegetable oil
Open this publication in new window or tab >>Enhancing UV protection of clear coated exterior wood by reactive UV absorber and epoxy functional vegetable oil
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Since ancient times wood has played a large role in human activities, both in terms of fuel and for construction purposes. A drawback with wood in exterior applications is, however, its susceptibility to photo-initiated degradation, caused by radiation from the sun. Hence, wood needs to be protected against ageing by means of different surface treatments. The work presented in this thesis describes a possible method for protecting wood against photo-initiated degradation. The system comprises the UV absorber, 2-hydroxy-4(2,3-epoxypropoxy)-benzo-phenone (HEPBP), which has a primary epoxy group with the ability to react covalently with hydroxyl groups, enabling reaction with hydroxyl groups of the wood (preferably phenolic hydroxyls in lignin). The epoxy functional vegetable oils (soybean and linseed oil) contain secondary epoxy groups which theoretically also enables reaction with the hydroxyl groups of the wood. This ability and a possible reaction with wood could result in a more long term protection since it prevents leaching of the protective substances. The study includes evaluation of several reaction parameters of the pretreatment, such as temperature, time, the influence of the oil, and also the photo protective ability of the sole pretreatment. The results show that a reaction temperature of 102 °C or higher results in presence of the reactants on the surface even after extraction, indicating grafting. Two different reaction procedures imply that reaction for 16 h results in slightly better results compared to a 1 h dipping procedure with 2 h subsequent drying in an oven. However, in terms of time and energy consumption the difference is considered too small to defend using the longer reaction procedure. Colour measurements of samples before, during and after ageing indicate a better performance of the pretreated samples compared to the untreated, and an effect of the oil is also noticed, giving the colour change a more stable increase that levels off instead of continuing to increase. The study also takes into account the use of a clear coating together with the pretreatment to study the performance of a complete coating system, in terms of photo protection. Coating of the pretreated samples is shown to work, with uncompromised adhesion as a result. Evaluations of natural and accelerated weathering of the full systems indicate only minor degradation after 1400 h of accelerated ageing or 14 months of natural exposure. After 4000 h of accelerated ageing, visible signs of degradation are detected, but the pretreated samples perform slightly better than the untreated. After 26 months of natural exposure the samples had too much mould in order to perform a reliable evaluation of the photo induced degradation. Overall the pretreatment is concluded to have a photostabilising effect of the wood.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2014. 87 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:46
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-156085 (URN)978-91-7595-318-2 (ISBN)
Public defence
2014-12-12, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
Formas, 2008-1447
Note

Resarch funder: Lantmännens Forskningsstiftelse. QC 20141121

Available from: 2014-11-21 Created: 2014-11-20 Last updated: 2014-11-21Bibliographically approved

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